Information on EC 1.14.14.15 - (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase

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The expected taxonomic range for this enzyme is: Streptomyces globisporus

EC NUMBER
COMMENTARY hide
1.14.14.15
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RECOMMENDED NAME
GeneOntology No.
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FADH2 + O2 = (3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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Biosynthesis of enediyne antibiotics
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SYSTEMATIC NAME
IUBMB Comments
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2],FADH2:oxygen oxidoreductase (5-hydroxylating)
The enzyme from the bacterium Streptomyces globisporus is involved in the biosynthesis of the (S)-3-chloro-5-hydroxy-beta-tyrosine moiety prior to incorporation into the chromoprotein antitumor antibiotic C-1027.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the enzyme is involved in the biosynthesis of the (S)-3-chloro-5-hydroxy-beta-tyrosine moiety prior to incorporation into the chromoprotein antitumor antibiotic C-1027
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FADH2 + O2
(3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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?
(R)-alpha-tyrosyl-[SgcC2] + FADH2 + O2
?
show the reaction diagram
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SgcC3 can utilize both (S)- and (R)-alpha-tyrosyl-[SgcC2] but not 3-hydroxy-alpha-tyrosyl-[SgcC2] as a substrate
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?
(S)-alpha-tyrosyl-[SgcC2] + FADH2 + O2
?
show the reaction diagram
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SgcC3 can utilize both (S)- and (R)-alpha-tyrosyl-[SgcC2] but not 3-hydroxy-alpha-tyrosyl-[SgcC2] as a substrate
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?
beta-aminoacyl-S-SgcC + FADH2 + O2
?
show the reaction diagram
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?
S-((3S)-3-amino-3-(3-bromo-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-bromo-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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-
?
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
S-((3S)-3-amino-3-(3-fluoro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-fluoro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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?
S-((3S)-3-amino-3-(3-iodo-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-iodo-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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?
S-((3S)-3-amino-3-(3-methyl-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-methyl-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FADH2 + O2
(3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
-
-
-
-
?
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
show the reaction diagram
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the enzyme is involved in the biosynthesis of the (S)-3-chloro-5-hydroxy-beta-tyrosine moiety prior to incorporation into the chromoprotein antitumor antibiotic C-1027. FADH2 is supplied by the C-1027 pathway-specific flavin reductase SgcE6
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?
additional information
?
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SgcC3 also efficiently catalyzes bromination but not fluorination or iodination
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
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dependent on
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.742
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2]
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pH 6.0, 25°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.023
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2]
Streptomyces globisporus
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pH 6.0, 25°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.031
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2]
Streptomyces globisporus
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pH 6.0, 25°C
29150
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 7
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pH 5.5: about 50% of maximal activity, pH 7.0: about 50% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
63200
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x * 63200, calculated from sequence, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 63200, calculated from sequence, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA agarose column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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overproduced as an N-terminal His6-tagged fusion protein
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